292053-98-6

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester
• CAS NO: 292053-98-6
• Molecular Weight: 1043.49
• Mol File: 292053-98-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(292053-98-6)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(292053-98-6)

Safety Data

• Hazardous Substances Data: 292053-98-6(Hazardous Substances Data)

Upstream product

• 56893-27-7 2-(3-(9-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)ureido)-3-hydroxybutanoic acid 
• 7387-57-7 triacetyladenosine 
• 33422-70-7 ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate 
• 292054-00-3 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 292053-99-7 5'-O-(4,4'-dimethoxytrityl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 58-61-7 adenosine 
• 292053-97-5 (2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 292053-96-4 C₂₇H₄₀N₆SiO₁₁SiC₆H₁₄ 
• 292053-91-9 N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 292053-90-8 (2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine 

Relevant articles and documents

Efficient access to 3′-: O -phosphoramidite derivatives of tRNA related N 6-threonylcarbamoyladenosine (t6A) and 2-methylthio- N 6-threonylcarbamoyladenosine (ms2t6A)

An efficient method of ureido linkage formation during epimerization-free one-pot synthesis of protected hypermodified N6-threonylcarbamoyladenosine (t6A) and its 2-SMe analog (ms2t6A) was developed. The method is based on a Tf2O-mediated direct conversion of the N-Boc-protecting group of N-Boc-threonine into the isocyanate derivative, followed by reaction with the N6exo-amine function of the sugar protected nucleoside (yield 86-94%). Starting from 2′,3′,5′-tri-O-acetyl protected adenosine or 2-methylthioadenosine, the corresponding 3′-O-phosphoramidite monomers were obtained in 48% and 42% overall yield (5 step synthesis). In an analogous synthesis, using the 2′-O-(tert-butyldimethylsilyl)-3′,5′-O-(di-tert-butylsilylene) protection system at the adenosine ribose moiety, the t6A-phosphoramidite monomer was obtained in a less laborious manner and in a remarkably better yield of 74%.